The Undertaker’s 10 Greatest Wrestlemania Matches

Mark Calaway (The Undertaker) is considered the greatest performer in the ring of all time. He’s been wrestling since 1991 and still does in terrific fashion. For those that don’t know, The Undertaker went undefeated at Wrestlemania until a couple years ago. His streak is considered legend; it stands at 23 wins and 1 loss. This list will count down the ten greatest matches of The Undertaker at Wrestlemania.

10. The Undertaker vs. Brock Lesnar – Wrestlemania 30: 21 – 1

Starting the list, we may as well start with the match that ended the streak. Brock Lesnar is a man who could probably tear a car apart with his hands (and he has). Returning in 2012 to feud with Cena, Brock went on head to head with The Undertaker in 2014 at Wrestlemania. Nobody actually expected Lesnar to beat the streak as there were more deserving talent. The Undertaker was concussed midway through the match but still fought on. Lesnar hit his finishing move, the F5, and that’s all she wrote. The crowd couldn’t believe it, I couldn’t believe it, the streak had come to an end. It was perfect.

Nobody wants to admit that the streak ending at Wrestlemania 30 was a good idea. Calaway had wanted to end the streak for almost a decade and they finally allowed him to do so. Calaway claimed that he wanted a younger talent to end the streak, that isn’t exactly what happened. But it was still a hell of a match. The feud was built up well. Paul Heyman at ringside at the end of the match just said it all. The face of pure shock and the scream of “Oh my God, you did it!”

9. The Undertaker vs. Triple H – Wrestlemania 27: 19 – 0

And now for a quick flashback to ten years ago. A fresh looking man called “Hunter Hearst Helmsley” was defeated by The Undertaker at Wrestlemania 17. Now here he is ten years later, being defeated by The Undertaker just with a different name.

A no holds barred contest saw Triple H completely dominate the majority of the match. The announce table was destroyed, chairs were bent and sledgehammers were smacked into faces. Overall, it was The Undertaker that prevailed with a submission move after nearly half an hour of back and forth action.

This match really overshadowed the rest of the event, especially that horrific main event we refuse to speak of. It set up a third match between the two at next years Wrestlemania and that one was just as good. We’ll get to that later though.

8. The Undertaker vs. Shane McMahon – Wrestlemania 32: 23 – 1

The most recent (and possibly final) match of The Undertaker was a match that put everything on the line. Shane returned and challenged his father for control of Raw. If he beat an opponent at Wrestlemania, he would gain control. Vince picked The Undertaker as Shane’s opponent, and the rest is history.

But how was everything on the line? Well if Shane won, he would gain control of Raw, but The Undertaker would never compete at Wrestlemania again. If The Undertaker won, it would be the opposite of that result. A match that saw Shane McMahon jump from the top of the cell and land through a table, it was iconic. Why was it iconic? Because it proved that two men who had been wrestling for years still had a lot of gas left in the tank. They’re still able to perform astonishing matches and that is exactly what they’ll continue to do.

7. The Undertaker vs. CM Punk – Wrestlemania 29: 21 – 0

This is a feud got really personal. Around this time, The Undertaker’s long time manager and friend, Paul Bearer, passed away. To add heat to the feud, Punk began to kayfabe disrespect Paul Bearer and The Undertaker.

The now UFC fighter CM Punk fought The Phenom in his final undefeated match at Wrestlemania 29. The bout itself was very fun and entertaining. The two men in the ring gave it their all and put on an impressive match. Paul Heyman accompanied Punk as it was at this time he was declared a “Paul Heyman” guy.

At times in the match, CM Punk would gain the upper hand and I was just thinking “this is it, it’s over”. But somehow The Undertaker managed to prevail and add another tally to his streak.

6. The Undertaker vs. Triple H – Wrestlemania 28: 20 – 0

Remember how I said HHH and Taker had a third match? Well, that was most certainly their best. Shawn Michaels took the position of special guest referee for the match. Michaels is a legend of the business, he’d retired after a match with Taker just two years prior, and now he was officiating a match with his best friend (HHH) taking on the man who ended his career. It wasn’t that simple though, we see the conflict Michaels has throughout the match. He has tremendous respect for The Undertaker, but Triple H and him have been best friends for years.

This is portrayed perfectly throughout the match. Especially when Hunter yells “You end it, or I will” at Michaels. He then proceeds to smack up everyone with a chair.

The ending of the match was perfect, Michaels and Hunter both hit their finishing moves on Taker. Taker kicked out, performed a tombstone and the three men just sat in the ring for a bit. It was the perfect end to a phenomenal, half hour match and it most certainly should have been the main event.

5. The Undertaker vs. Batista– Wrestlemania 23: 15 – 0

The first title match on this list as we’re heading back to a time when The Undertaker was still a full time competitor. A World Heavyweight title match between The Deadman and Batista. It was a brilliant match overall. Batista looked like he had the match won after he sent The Undertaker through the announce table. But again, The Undertaker prevailed with his finishing move The Tombstone.

Again the build up to this match was fantastic and the two had been feuding prior to their match at Wrestlemania. Batista did not manage to defend his title however and The Undertaker walked out with a championship belt in hand.

4. The Undertaker vs. Randy Orton – Wrestlemania 21: 13 – 0

Let us all go on a trip. Back to when Randy Orton wasn’t a boring heel. Oooooh, that was a burn now wasn’t it. Anyway, when he wasn’t busy listening to the voices in his head, Orton was busy decimating WWE Legends. His “Legend Killer” gimmick was truly fantastic and we saw him go up against legends like Shawn Michaels, Mick Foley, Hulk Hogan and even Dusty Rhodes. But nothing compared to his feud with The Phenom.

With a great back and forth match that even saw “Cowboy” Bob Orton interfere, The Deadman prevailed, once again using his finishing move The Tombstone. Randy Orton was, at the time, the man the WWE had picked to be the next face of the company. If anyone was to benefit by ending the streak, it would have been Orton. So why didn’t he end the streak? Orton had too much respect and refused to end the streak, which is very commendable and really does show that the feuds we see don’t continue over to reality.

3. The Undertaker vs. Shawn Michaels – Wrestlemania 25: 17 – 0

Shawn Michaels and The Undertaker can be considered the two greatest wrestlers in the business. Their two Wrestlemania matches were legendary. Their first bout appeared at Wrestlemania 25 in a half hour match. They both put it all on the line in this match. As you can see in the photo above, a lot of high risk moves were performed, and a lot of camera men were hit with said moves.

This match will be remembered as one of the greatest matches of all time, but two other matches have managed to top this spectacle.

The Undertaker vs. Edge – Wrestlemania 24: 16 – 0

Another title match now, which saw The Ultimate Opportunist go up against The Deadman. Now maybe I’m biased because I’m an Edge fan, but this was the best match on the card. It was so good in fact that it was the main event of the show, and rightly so.

A feud between the two lasted months and months, finally coming to an end at Hell in a Cell with Edge prevailing. But it’s their match at Wrestlemania that everyone remembers the most. With an interference by Curt Hawkings and Zack Ryder, The Undertaker still prevailed with a win over Edge by submission. It’s close to being the greatest Wrestlemania match with The Undertaker, but it just misses out on that spot by one other match.

Just a quick honourable mention now. Mark Henry vs. The Undertaker may be an odd choice, but just hear me out on this one. It was the only casket match to ever appear in The Undertakers Wrestlemania career. It was against Mark Henry, who isn’t the most memorable opponent, but at least it isn’t Giant Gonzalez.

1. The Undertaker vs. Shawn Michaels – Wrestlemania 26: 18 – 0

The match that ended Michaels’ wrestling career. But a phenomenal match at that. What makes this the greatest Undertaker Wrestlemania match though? Streak vs. Career. The Phenom vs. Mr. Wrestlemania. It was built up for well over a year after what happened at the previous Wrestlemania.

An almost twenty minute match, that ended with a pinfall victory over HBK and the end of a career. However what was interesting is what happened after the match. The Undertaker has only broken character maybe once or twice. The first to pay his respects to a retiring Ric Flair, the second being at the end of this match, to give a warm handshake and a hug to Shawn Michaels.

That is why it is the best match. Because these two men gave it their all and they had huge amounts of respect for each other, which lead to The Undertakers greatest Wrestlemania match to this date.